10-phenylmethoxydecan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 7 g of 10-benzyloxy-1-decanol, 8 ml of thionyl chloride, and 0.2 ml of dimethylformamide was heated to 50° to 60° C. for one hour. After the reaction was over, the reaction mixture was concentrated under reduced pressure, the residue was dissolved in 50 ml of n-hexane, and after washing the solution with water, the solution was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off and the residue was applied to silica gel column chromatography and eluted with toluene to provide 6.7 g of oily 10-benzyloxy-1-chlorodecane. Boiling point 135°-140° C. (0.6-0.9 mm Hg). was heated to 50° to 60° C. for one hour was concentrated under reduced pressure the residue was dissolved in 50 ml of n-hexane after washing the solution with water the solution was dried over anhydrous magnesium sulfate Then, the solvent was distilled off eluted with toluene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 7 g of 10-benzyloxy-1-decanol, 8 ml of thionyl chloride, and 0.2 ml of dimethylformamide was heated to 50° to 60° C. for one hour. After the reaction was over, the reaction mixture was concentrated under reduced pressure, the residue was dissolved in 50 ml of n-hexane, and after washing the solution with water, the solution was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off and the residue was applied to silica gel column chromatography and eluted with toluene to provide 6.7 g of oily 10-benzyloxy-1-chlorodecane. Boiling point 135°-140° C. (0.6-0.9 mm Hg). was heated to 50° to 60° C. for one hour was concentrated under reduced pressure the residue was dissolved in 50 ml of n-hexane after washing the solution with water the solution was dried over anhydrous magnesium sulfate Then, the solvent was distilled off eluted with toluene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of decane-1,10-diol (3 g, 17.21 mmol), benzyl bromide (2.25 ml, 18.94 mmol) and Ag2O (5.98 g, 25.82 mmol) in dry DCM (50 ml) were added, the reaction mixture was refluxed overnight, then the Ag2O was filtered off. The crude product was purified by silica gel column (10% EtOAc in Hexane) to afford 10-(benzyloxy)decan-1-ol as a gummy colorless liquid (2.96 g, 65%). were added the reaction mixture was refluxed overnight the Ag2O was filtered off The crude product was purified by silica gel column (10% EtOAc in Hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of decane-1,10-diol (3 g, 17.21 mmol), benzyl bromide (2.25 ml, 18.94 mmol) and Ag2O (5.98 g, 25.82 mmol) in dry DCM (50 ml) were added, the reaction mixture was refluxed overnight, then the Ag2O was filtered off. The crude product was purified by silica gel column (10% EtOAc in Hexane) to afford 10-(benzyloxy)decan-1-ol as a gummy colorless liquid (2.96 g, 65%). were added the reaction mixture was refluxed overnight the Ag2O was filtered off The crude product was purified by silica gel column (10% EtOAc in Hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, m/e=405.6 ([M−H]−), was produced in analogy with example 1, steps 1 to 4. Thus, 1,10-decanediol was alkylated in step 1 with benzyl bromide, leading to 10-benzyloxy-decan-1-ol, which was oxidized in step 2 to 10-benzyloxydecanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-3-(10-benzyloxy-decanoylamino)-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.